The Bet

I drove around and around until I had reached the 8th floor of the parking garage, and started looking for section 8F as instructed. My girlfriend and I like to play a game where we bet on random meaningless things, like who will be get ousted in the episode of a TV reality show. Whoever wins, gets to call the shots on our next weekend getaway or vacation. It actually works out great. No vacation arguments about where to eat or what to do. Its actually nice to lose sometimes and just go with the flow. This time, I lost. Who knew that girl would slip and fall on that dancing show?

I found the right section, and saw my girlfriend's car already parked. I found a spot right next to her as this entire area was empty. This time of year, not enough travelers to need to park this far from the terminal.

I didn't even know where we were flying to. That was part of the game. She made all the arrangements. Like I said, losing isn't all that bad. She did tell me to bring some nice slacks and shirts, but to be prepared for warm weather, and to pack light. I got out of my car, popped the trunk, and pulled out my small roller bag and my carry-on with a change of clothing—just in case.

Sarah got out of her car when she saw me park, and was doing the same thing. Her bag was much larger. I never understand how a woman can pack so much for such a short trip, but I knew better than to comment. I walked over to help her with the bag, and was about to ask why we were parked way out in this section when she spoke, "sweetie, before we get going, I have something for you to wear. The game starts now." A twinkle in her eyes made me realize that she had something up her sleeve.

She reached into her trunk and pulled out a small pink Victoria's Secret bag and handed it to me. I took it, and immediately started feeling flush. I always fawn over her sexy lingerie, sometimes even asking her to leave it on while we have sex. I love the soft silky fabrics and sexy lace. I once confessed to her that I fantasized about what it would feel like to wear panties.

"That's for you to wear. You'll need to put them on right here. I can help you," she said in a very conversational way, like how's the weather? I was looking in the bag, and I could see a pair of hot pink satin panties with lace trim.

"uh,...what?" I asked, a bit confused, "here?...but..."

"Don't worry silly, why do you think I asked you to park all the way out here? Afterall, the game is afoot, and I make all the decisions. I decided that you should wear these," she explained.

I pulled the panties out of the bag, and noticed that they were not the only thing in the bag. A black butt plug sat nestled in the tissue paper of the bag. The look of surprise must have shown on my face, because I heard her giggle. I looked at her, and I began to protest when she cut me off.

"Don't forget who's in charge here. As a matter fact, you may as well start getting used to calling me Mistress. You got that pantyboy?"

"Er...yeah, no problem Sar- I mean Mistress."

She spoke with a new-found authority that I had never seen before, but I could feel my cock twitch with excitement. I stepped out of my shoes, took one last look around, and started to take off my pants. When I was naked from the waist down, she ordered me to lean up against the trunk of my car and "spread 'em". She sounded like she was having fun. I, on the other hand, was weirdly excited and freaked out. While I was trying to comprehend what was going on, and what this woman had done with my Sarah, I felt a cold wet finger on my anus.

"Ah!" I yelped as she pushed a finger inside me. At least, I realized, she was using some lube. I had never used a butt plug, nor had I ever even expressed an interest about it to Sarah. The panties, yes, butt plug, no. Everything seemed so surreal, and just like that, I felt something cold and hard pushing against my anus. The plug started pushing into me, and I immediately realized why so many women will not let men fuck them in the ass. The plug was a medium sized plug. It had looked like it was probably about 5 inches long and at most an inch or slightly more at its widest point. It felt, however, like a baseball bat pushing into my ass. I heard someone scream, and then realized it was me. All I could see was bright light. I've endured more pain, but it was enough that I really couldn't think. Then, I felt a pop, and the pain receded. The widest part had pushed into me, and now a dull ache was left behind along with a feeling of fullness that I had never felt before.

"Step into these. You better hurry, I think I hear a car."

With those words, I returned to lucid thought, and I remembered where I was standing. Looking down, I could see she was holding the panties by my feet. I stepped into them, and she pulled them up my legs. She reached around, and adjusted my cock so that the satin fabric cupped my balls and contained my cock. The smooth light satiny fabric was as luxurious as I had imagined.

"Hey pantyboy, gonna put these on? Or are you good like that?"

Sarah was holding my pants out to me. I took them, put them on, and then got my shoes and socks on. While I was finishing tying my shoes, Sarah had tossed my boxers into her trunk, closed the trunk, and stood waiting for me with our luggage. I stood back up, and started to walk to her when I felt the plug shift inside me. It sent waves of pleasure right through to my cock. I had to focus to keep walking straight.

"Come on pantyboy, get our luggage and let's get going. We have a flight to catch. And don't forget to wave to the camera." She started walking toward to elevators and held up her hand, finger pointing at the ceiling. I looked up and saw a security camera pointed right at me, little red light blinking. I immediately looked back down, hoping my face wasn't too clearly framed on the camera, grabbed the bags, and followed Sarah as quickly as the plug would allow.

With each step, I could feel the plug shifting inside me. It didn't help that I was now developing a hard on. Between the plug and the satin panties, my body and my mind were getting turned on. I tried to use my carry-on to shield my excitement, clutching it in front of my pelvis. As we finally reached the main terminal, I was hoping that I had mastered walking as I kept telling myself that busy travelers were not going to pay attention to a guy who looked like he had a stick up his ass — which I immediately realized was a more than accurate assessment of my situation.

Sarah took charge, and checked us in at the self-check in kiosk. We checked our luggage and headed for the gate. Sarah barely looked at me, striding confidently down the concourse. As we neared the security checkpoint, I started feeling more and more uncomfortable. It wasn't the plug that was sending waves of pleasure through me with each step, but as i neared the checkpoint, i had a flash of being strip searched by a TSA guard who some how knew that i had something "hidden".

"Ah Sarah, wait please," I pleaded. Sarah turned to face me, and gave me a look of warning. "Sorry, Mistress, please wait. Can I get through security like this?" I asked motioning with my eyes downward to my midsection. At least by now, my cock had settled down, and was no longer tenting my pants.

"Silly boy, they don't xray you, and they wouldn't be able to see the panties ayway. And the plug is not metal. It won't be a problem, now come, we have a plane to catch." And with that, she turned and kept walking into the roped-off lines of security. By the looks of some nearby travelers, it was clear that they heard that exchange. I could feel my face turning red.

I took a deep breath, let it out, and followed her. She was right of course, but that didn't stop my heart from racing as I went through security. One TSA guard looked at me, clearly noticing that I was fidgeting. Crap, I realized showing strange nervousness could make one of them think that I was doing something illegal. I smiled weakly to the guard, "Hi. I hate flying," I said in a poor attempt at an excuse. She rolled her eyes, and just reached for my boarding pass, looked at it, and waved me on.

I followed Sarah down the concourse to our gate, and we found a place to sit. I was so glad to be able to sit down and stop walking, I completely forgot what would happen when I did sit. So I sat, and immediately realized my mistake as the plug pushed hard up into me, filling me deeper than before. I stifled a yelp, and tried to look at the floor as if nothing had happened. I peeked over at Sarah, knowing she was probably glaring at me. She was.